Identification
NameLincomycin
Accession NumberDB01627
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

Structure
Thumb
Synonyms
LCM
Lincomycine
External IDs U-10,149 / U-10149
Product Ingredients
IngredientUNIICASInChI KeyDetails
Lincomycin hydrochlorideGCW8Y9936L 859-18-7POUMFISTNHIPTI-BOMBIWCESA-NDetails
Lincomycin hydrochloride monohydrateM6T05Z2B68 7179-49-9LFZGYTBWUHCAKF-DCNJEFSFSA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LincocinCapsule500 mgOralPfizer1964-12-312006-08-02Canada
LincocinInjection, solution300 mg/mLIntramuscular; Intravenous; SubconjunctivalPharmacia & Upjohn Inc1964-12-29Not applicableUs
LincocinSolution300 mgIntramuscular; IntravenousPfizer1964-12-312016-05-06Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LincomycinInjection, solution300 mg/mLIntramuscular; Intravenous; SubconjunctivalX Gen Pharmaceuticals, Inc.2015-07-05Not applicableUs
LincomycinInjection, solution300 mg/mLIntramuscular; Intravenous; SubconjunctivalX Gen Pharmaceuticals, Inc.2015-07-05Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
LincobectNot Available
LincorexNot Available
Brand mixturesNot Available
Categories
UNIIBOD072YW0F
CAS number154-21-2
WeightAverage: 406.54
Monoisotopic: 406.213757997
Chemical FormulaC18H34N2O6S
InChI KeyOJMMVQQUTAEWLP-KIDUDLJLSA-N
InChI
InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
IUPAC Name
(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidic acid
SMILES
Pharmacology
Indication

Lincomycin is an antibiotic used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

Structured Indications
Pharmacodynamics

Lincomycin is a lincosamide antibiotic that comes from the yeast Streptomyces lincolnensis. Lincomycin has been shown to be active in vitro against the following microorganisms: Aerobic gram-positive cocci: Streptococcus pyogenes and Viridans group streptococci; Aerobic gram-positive bacilli: Corynebacterium diphtheriae; Anaerobic gram-positive non-sporeforming bacilli: Propionibacterium acnes; Anaerobic gram-positive sporeforming bacilli: Clostridium tetani and Clostridium perfringens.

Mechanism of action

Lincomycin inhibits protein synthesis in susceptible bacteria by binding to the 50 S subunits of bacterial ribosomes and preventing peptide bond formation upon transcription. It is usually considered bacteriostatic, but may be bactericidal in high concentrations or when used against highly susceptible organisms.

TargetKindPharmacological actionActionsOrganismUniProt ID
50S ribosomal protein L10Proteinyes
inhibitor
Shigella flexneriP0A7J6 details
Related Articles
Absorption

Rapidly absorbed from the gastrointestinal tract following oral administration. Approximately 20 to 30% absorbed orally in fasting state; absorption decreased when taken with food.

Volume of distributionNot Available
Protein binding

Protein binding decreases with increased plasma concentrations. Range, 28 to 86% (average, 70 to 75%). Albumin is not thought to be the primary binding component.

Metabolism

Presumed hepatic, however metabolites have not been fully characterized.

Route of elimination

Urinary excretion after this dose ranges from 1.8 to 24.8 percent (mean: 3 percent). Tissue level studies indicate that bile is an important route of excretion.

Half life

The biological half-life after intramuscular or intravenous administration is 5.4 ± 1.0 hours. The serum half-life of lincomycin may be prolonged in patients with severe impairment of renal function compared to patients with normal renal function. In patients with abnormal hepatic function, serum half-life may be twofold longer than in patients with normal hepatic function.

ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Lincomycin Action PathwayDrug actionSMP00728
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Lincomycin.Investigational
DoxofyllineThe serum concentration of Doxofylline can be increased when it is combined with Lincomycin.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Lincomycin.Approved
Food Interactions
  • Take on an empty stomach, food decreases absorption.
References
Synthesis Reference

Alexander D. Argoudelis, David W. Stroman, "Process of producing lincomycin nucleotides." U.S. Patent US4464466, issued June, 1972.

US4464466
General ReferencesNot Available
External Links
ATC CodesJ01FF02 — Lincomycin
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableInfections, Bacterial1
1CompletedOtherHealthy Male Chinese Volunteers1
1CompletedOtherHealthy Male Volunteers1
1CompletedTreatmentHealthy Volunteers1
2CompletedPreventionMigraines1
2CompletedTreatmentNonconvulsive Seizures1
3Active Not RecruitingTreatmentEpilepsies1
3CompletedTreatmentEpilepsies1
4Active Not RecruitingTreatmentCellulitis1
4CompletedTreatmentEpilepsy, Localization Related1
Not AvailableCompletedNot AvailableFocal Epilepsy With and Without Secondary Generalization1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral500 mg
SolutionIntramuscular; Intravenous300 mg
Injection, solutionIntramuscular; Intravenous; Subconjunctival300 mg/mL
Prices
Unit descriptionCostUnit
Lincocin 300 mg/ml vial7.79USD ml
Lincomycin hcl powder3.29USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.56HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.02 mg/mLALOGPS
logP0.34ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)8.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.98 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.19 m3·mol-1ChemAxon
Polarizability43.91 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5937
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7945
P-glycoprotein inhibitor INon-inhibitor0.6755
P-glycoprotein inhibitor IINon-inhibitor0.5633
Renal organic cation transporterNon-inhibitor0.8868
CYP450 2C9 substrateNon-substrate0.8417
CYP450 2D6 substrateNon-substrate0.8837
CYP450 3A4 substrateSubstrate0.6389
CYP450 1A2 substrateNon-inhibitor0.9222
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9269
CYP450 2C19 inhibitorNon-inhibitor0.9203
CYP450 3A4 inhibitorNon-inhibitor0.9342
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.7696
CarcinogenicityNon-carcinogens0.9482
BiodegradationNot ready biodegradable0.9622
Rat acute toxicity2.5777 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9847
hERG inhibition (predictor II)Non-inhibitor0.7163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (7.07 KB)
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000j-0900000000-1f46f29c3d5dbc6c25f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0901000000-3fc103447a71fd95ceddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-016r-0895000000-4b0507fffd39d9fc075fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00mk-0952000000-ca2f735ea2244e1cb32eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0901200000-cc68fda14967bfcd7357View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-70466cfb7e0692d073a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-b712dc39bbf605193fb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0109000000-cdbfa33f16a571dd85eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0209000000-8ec5c595eb6720c93c13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative ParentsAlpha amino acid amides / Thioglycosides / Pyrrolidinecarboxamides / Monosaccharides / N-alkylpyrrolidines / Oxanes / Monothioacetals / Trialkylamines / Secondary carboxylic acid amides / Secondary alcohols
SubstituentsProline or derivatives / Alpha-amino acid amide / Glycosyl compound / S-glycosyl compound / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Monosaccharide / Oxane / N-alkylpyrrolidine / Monothioacetal
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptorsmonocarboxylic acid amide, pyrrolidinecarboxamide, L-proline derivative, carbohydrate-containing antibiotic, S-glycosyl compound (CHEBI:6472 )

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a central role in the interaction of the ribosome with GTP-bound translation factors.
Gene Name:
rplJ
Uniprot ID:
P0A7J6
Uniprot Name:
50S ribosomal protein L10
Molecular Weight:
17711.38 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Odom OW, Hardesty B: Use of 50 S-binding antibiotics to characterize the ribosomal site to which peptidyl-tRNA is bound. J Biol Chem. 1992 Sep 25;267(27):19117-22. [PubMed:1527036 ]
  3. Champney WS, Tober CL: Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics. Curr Microbiol. 2000 Aug;41(2):126-35. [PubMed:10856379 ]
Drug created on August 29, 2007 15:12 / Updated on September 01, 2017 10:42